Diane Prince sold her staffing firm for $28 million and discovered something counterintuitive: the biggest business killers aren't market conditions or competition. They're the psychological traps entrepreneurs set for themselves. Her raw advice cuts through entrepreneurial fantasy and delivers the mindset shifts that actually move the revenue needle.
In this episode we talk about the sunk cost fallacy that keeps founders throwing good money after bad, why perfectionist control freaks can't scale past themselves, and the offshore team management system that turns virtual assistants into revenue drivers. Prince breaks down her modified EOS approach, explains why most tool purchases are expensive mistakes, and reveals the uncomfortable truth about holding onto wrong-fit employees.
Key Takeaways
➡ Sunk cost fallacy is the business killer: Stop doing what's not working regardless of investment
➡ Prince's client spent $250K building a custom ATS when Bullhorn already did the job
➡ Wrong people cost more than their salaries: They drag down your entire team's performance
➡ Perfectionism prevents scaling: Things won't be perfect even when you do them yourself
➡ One extra $30K placement covers an entire virtual assistant team for a year
➡ 75% of entrepreneurs don't know their breakeven point or if they're profitable
➡ Leadership must use the tools they buy: If you're not in the system, your team won't be either
➡ Vision assessment every 90 days: Your why can change, and that's okay
➡ Global talent misconception: Treating offshore workers as individuals, not geography stereotypes
Chapters
00:00 – Intro and Diane's Background
02:47 – The $28M Sale Story
05:06 – Sunk Cost Fallacy Lesson
08:04 – Why Entrepreneurs Keep Failing
12:13 – Offshore Team Management
20:30 – Delegation Mindset Shifts
23:08 – EOS System Modifications
28:53 – Technology Tool Trap
36:41 – Scaling Uncomfortable Truths
40:17 – Business Timing Questions
46:48 – Common Leadership Blind Spots
Sound Bites
"If something is not working, stop doing it no matter what you've invested in it. You're always starting from scratch."
"I hired someone from India and it was a disaster, so I'm never doing it again is the same as saying I hired someone from Texas and I'm never hiring from Texas again."
"Salespeople who haven't done a deal in a year while founders aren't paying themselves because they feel guilty."
Guest InfoName: Diane PrinceWebsite: dianeprince.coLinkedIn: https://www.linkedin.com/in/dianeprincejohnston/
Expertise: Business acceleration coach specializing in staffing agencies and offshore team building